CNDE
The enantioselective biocatalytic hydrolysis of rac-2-carboxyethyl-3-cyano-5-methylhexanoic acid ethyl ester to obtain a key (S)-intermediate is crucial for the synthesis of Pregabalin (a lipophilic 4-aminobutyric acid (GABA) analogue and has been developed to a new blockbuster drug for the treatment of several central nervous system disorders including neuropathic pain, epilepsy, anxiety and social phobia). It is also substrate of EstZF172 A0A0N7CSD6 from Psudomonas which is not an Alpha/beta hydrolase but a Beta-lactamase, family VIII Xu et al.
General
Type : Cyanide
Chemical_Nomenclature : 5-cyano-4-ethoxycarbonyl-7-methyloctanoic acid
Canonical SMILES : CCOC(=O)C(CCC(=O)O)C(CC(C)C)C#N
InChI : InChI=1S\/C13H21NO4\/c1-4-18-13(17)11(5-6-12(15)16)10(8-14)7-9(2)3\/h9-11H,4-7H2,1-3H3,(H,15,16)
InChIKey : MBZSCAJFNRHIKS-UHFFFAOYSA-N || MBZSCAJFNRHIKS-DTIOYNMSSA-N || MBZSCAJFNRHIKS-VUWPPUDQSA-N
Other name(s) : SCHEMBL2223205 || 2-carboxyethyl-3-cyano-5-methylhexanoic acid, ethyl ester || Rac-2-carboxyethyl-3-cyano-5-methylhexanoic acid ethyl ester || (+\/-)-2-carboxyethyl-3-cyano-5-methyl hexanoic acid ethyl ester || 2-(2-Carboxyethyl)-3-cyano-5-methylhexanoic acid 1-ethyl ester
MW : 255.31
Formula : C13H21NO4
CAS_number :
PubChem : 129826807, 129826810, 86583641
UniChem : MBZSCAJFNRHIKS-UHFFFAOYSA-N, MBZSCAJFNRHIKS-DTIOYNMSSA-N, MBZSCAJFNRHIKS-VUWPPUDQSA-N
Target
Structures : No structure
Families : Lipase_3
References (4)
| Title : Engineering of Talaromyces thermophilus lipase by altering its crevice-like binding site for highly efficient biocatalytic synthesis of chiral intermediate of Pregablin - Ding_2018_Bioorg.Chem_77_330 |
| Author(s) : Ding X , Zheng RC , Tang XL , Zheng YG |
| Ref : Bioorg Chem , 77 :330 , 2018 |
| Abstract : |
| PubMedSearch : Ding_2018_Bioorg.Chem_77_330 |
| PubMedID: 29421709 |
| Gene_locus related to this paper: talth-f6lqk7 |
| Title : Engineering of Thermomyces lanuginosus lipase Lip: creation of novel biocatalyst for efficient biosynthesis of chiral intermediate of Pregabalin - Li_2014_Appl.Microbiol.Biotechnol_98_2473 |
| Author(s) : Li XJ , Zheng RC , Ma HY , Zheng YG |
| Ref : Applied Microbiology & Biotechnology , 98 :2473 , 2014 |
| Abstract : |
| PubMedSearch : Li_2014_Appl.Microbiol.Biotechnol_98_2473 |
| PubMedID: 23917635 |
| Gene_locus related to this paper: thela-m4tp71 |
| Title : Biocatalytic synthesis of chiral intermediate of pregabalin with high substrate loading by a newly isolated Morgarella morganii ZJB-09203 - Zheng_2013_Appl.Microbiol.Biotechnol_97_4839 |
| Author(s) : Zheng RC , Wang TZ , Fu DJ , Li AP , Li XJ , Zheng YG |
| Ref : Applied Microbiology & Biotechnology , 97 :4839 , 2013 |
| Abstract : |
| PubMedSearch : Zheng_2013_Appl.Microbiol.Biotechnol_97_4839 |
| PubMedID: 23504060 |